I think destination is important but your company may matter more. If they are generous and supportive, it should be easier. Of course your position matters as well, everyone doesn’t get same perks. Your family’s flexibility and support too can make or break your plans.
Did 2 expat stints in 2 different countries in Asia over 8 years (not consecutive). Benefits and compensation were generous in both situations, with very nice housing paid for, COLA adjustment, tax equalization and preparation by a big accounting firm. I had the same payroll deduction for health insurance, but my company just footed 100% of any healthcare cost. The first stint, Tokyo, was not as enjoyable as the second stint, HK, primarily because the expat community seemed less active in Tokyo vs HK. I was also single during my Tokyo stint, but was newly married in my HK stint. For me, having someone to share the adventure with is a good thing and my wife was also able to secure a decent job on a local pay scale. We had both kids in HK, which was great as our live in housekeeper did double duty as a nanny. To this day she is still like a part of our family and we stay in close touch. Many of my expat friends never left. Others could not get out of there quickly enough. So, I think it is a question of how adventurous you are personally and how well your company takes care of you. HK (and Tokyo) may have been less enjoyable if I had to live in housing that locals generally lived in vs my relatively luxuries expat pads.
@brantly, my daughter was a Fulbright scholar to Denmark, earned her Master’s in wind energy there, and found her dream job in Copenhagen. I’m currently sitting at the Copenhagen airport after a two week visit with her. It was fascinating to see how she lives now, knowing how we raised her. She is totally comfortable with lifestyle changes that my husband and I could only tolerate temporarily. (We never mentioned anything to her.)
PM me if you want more details.
We have lived overseas for 22 years now. First three years was with a private organization, the past 19 for the US government, military related. We first went overseas in order to pay off our student loans after graduate school. With a housing benefit and day care benefit it was possible to pay down our loans very quickly. But, there were many things about the lifestyle that appealed to us and we continued. We had a friend who was a retired correspondent for Time Magazine who warned us before left the first time that once we tried this life we might never come back. We thought he was crazy, but here we are still in Asia. We’ve been able to achieve a lot of goals financially that would have been a lot harder if we stayed in Maine where we are from. We’ve seen a lot of the world. We’ve given up a lot too, family events and what not, things that aren’t practical to be a part of.
The truth is that overseas life can be an amazing short term thing, but then some of us who didn’t intend to spend a long time overseas end up making it a lifestyle. We are looking at short term at this point, two to three more years. The thought of returning for good is both exciting and scary. If it appeals to your son, it can be really great.
Currently a student in the US, but spent almost all of my life as an American overseas except for summer vacations. I sometimes feel like an expat in the US! I loved growing up in my host country and was able to learn to speak the language fluently (with a local accent, which makes me stand out when we visit more cosmopolitan areas than where we lived). I definitely developed some mannerisms of our host culture and still really miss the food. Luckily my parents still live there so they send boxes and boxes of provisions and I’ve learned to cook the local cuisine passably. My boyfriend had never left North America (he’s been to Canada) before my parents flew us to our host country for Christmas a couple of years back and now we both fantasize about living somewhere other than the US one day; I’m already exploring options in Europe for postdoc positions in English-speaking programs. There’s definitely something special about really living in a different country, and not just visiting.
As a child I lived as an expat during my elementary school years in the Indian subcontinent. My father worked for USAID. We moved back to the US as I entered junior high - I am the youngest and two of my brothers were in high school. The eldest finished HS in the US living with a grandmother and had started college.
I always feel fortunate for my upbringing and extensive travels as a child.
After we were all out of college, my parents moved to other places overseas: Egypt, the Philippines, and Saudi Arabia.
My D is now an expat in London. She sought a job transfer within her company and has been there a little over a year. She loves all the travel she can do and the experience of being in a new country.
I did it in my early thirties. H was from the country and it was his job. He worked for an American company that was part of a web of American companies operating abroad. Because he was from the country, it was easier for us. We did not live as cosseted in the expat community as others did. We moved between the local and expat communities.
I studied the language and got a bus pass. When H was at work, I was in class or exploring on my own. I handled all the day to day chores, like paying bills and dealing with repairmen.I made my own friends, who were mostly people like me, other ex pats or Americans who had chosen to live in the country. It was kind of lonely for me.
I had a baby there. That was my only exposure to the national health care system. It set a floor on care IMHO. Not as comfortable as in the US, but cheaper.
It was a valuable experience, but I was relieved to come back home. I was surprised how happy I was to return to the US, even though it was to a place I had never lived and had no friends. I was abroad for three years.
Not overseas but have lived in Canada for 45+ years. Great quality of life, universal healthcare, wonderful public education, affordable university, little crime, diverse population, belief in a social safety net for all. I would never return to the U.S. permanently.
Because HK was until recently a British colony I think their attitude about foreigners is quite different from most countries in Asia. It’s also a big center of international banking. I’d be a little leery of HK however, it seems pretty clear that China is pushing the boundaries of the 50 year agreement to let them govern themselves.
We had a very positive corporate expat experience. DH is not a high level exec, so it wasn’t a super pampered experience, but still very worthwhile. Kids were young (but out of diapers) and I think it had a very positive influence on them. Definitely opened them up to languages, cultures and traveling.
It can be hard to get off that path, though After one successful assignment, HR was like, “Hey - you didn’t have any family emergencies, or cost us a fortune in schooling, and we didn’t have to terminate the assignment early. So how about Dubai? Or UAE, or maybe China?”
DH, “Nah, I want to go back to the US.”
HR, “But we have such awesome positions available overseas.”
DH, “No thank you. I’m going back to the US.”
HR, “Ok. Hope you can network and find something…”
I think it could partially explain the comment from @BelmontVA commented about people continuing to do expat assignments. Even after we’d been back in the US, DH was presented another option in Italy. I tried really hard to convince him to take that one, but he didn’t want to do another overseas move in a matter of months. I still think of that one as the one that got away!
I will say that it was hard for my brother to come back to the US after so many years in Asia. He couldn’t get a compatible job he was doing in Asia. It took him quite a few years to re-establish himself again. His kids also had a hard time to assimilate to US live. The kids spoke perfect English, went to American International school, but it was still hard for them.
Best 6 years of my life. I would highly recommend it to anyone. I always wanted to work overseas, mainly just to experience another culture and see more of the world on somebody else’s dime (my employer). We traveled a lot when I was growing up. When I signed up for the expat job in my big bank I didn’t realize how lucrative it was. Company paid for everything - rent, utilities, club membership, trips home. We lived in HK for 3 years. Then moved to Tokyo. The cost of living adjustment in Japan was enough to live on allowing me to pretty much bank my salary. Remember, expenses were almost nil - groceries and some non business entertainment. I don’t think most expat packages today are as generous as mine was back then. I was not a top executive, but I had pretty much everything the office manager had except I didn’t have my own driver and company car. 
It was NOT great for my career. Having gained familiarity with Asian markets, after I returned to the U.S. I ended up using my specialized knowledge to work with Asian markets - so for the last 10 years of my work life I worked at night, during Asian hours.